Dabigatran etexilate and the tautomers, racemates, enantiomers, pharmacologically acceptable acid addition salts, solvates, hydrates and prodrugs thereof, particularly its acid addition salt with methanesulfonic acid being represented as compound of Formula (I).

The active compound dabigatran etexilate is known from international (PCT) publication WO 98/37075, wherein compounds with a thrombin-inhibiting and thrombin time prolonging activity are disclosed, under the name 1-methyl-2-[N-[4-(N-hexyloxycarbonylamidino)phenyl]-amino-methyl]-benzimidazol-5-yl-carboxylic acid-N-(2-pyridyl)-N-(2-ethoxycarbonylethyl)mide also known as BIBR 1048. The compound of Formula (I) is a double prodrug of the compound (E′).

Therefore, the compound of Formula (I) i.e. dabigatran etexilate mesylate is only converted into the active compound, namely the compound of Formula (E′), after entering the body. The main indication for the compound of chemical Formula (I) is the post-operative prevention of deep vein thrombosis and the prevention of strokes.
International (PCT) Publication WO 98/37075 discloses the process for the preparation of substituted (4-benzimidazol-2-ylmethylamino)benzamidines by reacting the corresponding, substituted (4-benzimidazol-2-ylmethylamino)benzonitriles with ammonia, i.e. the process for the preparation of dabigatran etexilate. This method is very tedious in terms of production costs and results in a high load of acids requiring disposal.
International (PCT) Publication WO 03/074056 A1 discloses acid addition salt of dabigatran etexilate with methanesulfonic acid.
U.S. Pat. No. 7,932,273 B2 discloses three polymorphic forms viz. Form I, Form II and hemihydrate forms of dabigatran etexilate mesylate characterized by x-ray powder diffraction and differential scanning calorimetry.
International (PCT) publication WO 2006/131491 discloses different polymorphic forms of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazole-5-carbonyl)-pyridin-2-yl-amino]-propionate i.e. dabigatran etexilate free base. In particular, the WO '491 discloses anhydrous Form I, anhydrous Form II and a tetrahydrate Form.
International (PCT) publication WO 2008/059029 A2 discloses anhydrous Form III, anhydrous Form IV, monohydrate Form I, monohydrate Form II, as well as nitrobenzene solvate of dabigatran etexilate free base.
U.S. Pat. No. 7,202,368 B2 discloses the process for preparing dabigartan etexilate. The process disclosed in the art involves cumbersome steps of column chromatography and the obtained intermediates are in residue form which results in low purity and yield of the product.
In view of the above, it is therefore, desirable to provide an efficient, economical and eco-friendly process for the preparation of dabigatran etexilate mesylate. In particular, the present inventors have found novel crystalline form of intermediates of Formula 2A, Formula 2B and Formula E having good physiochemical properties and useful for further processing.
Therefore, the present invention provides novel crystalline form of intermediates of dabigatran etexilate. In particular, the present invention provides crystalline form of compound ethyl 3-(3-amino-4-(methylamino)-N-(pyridin-2-yl)benzamido)propanoate of Formula 2A, ethyl 3-(2-((4-cyanophenylamino)methyl)-1-methyl-N-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxamido) propanoate, of Formula 2B and 1-methyl-2-[N-(4-amidinophenyl)aminomethyl]benzimidazol-5-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide hydrochloride of Formula (E) as well as its process of their preparation and use thereof for the preparation of dabigatran etexilate mesylate.